catena-Poly[[aqua­trimethyl­tin(IV)]-{[trimethyl­tin(IV)]-μ3-thio­phene-2,5-dicarboxyl­ato}]

Yang, S.-X.; Li, Y.-Z.; Jiang, K.

doi:10.1107/S1600536808043614

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m137

doi:10.1107/S1600536808043614

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catena-Poly[[aquatrimethyltin(IV)]-{[trimethyltin(IV)]-μ₃-thiophene-2,5-dicarboxylato}]

Sheng-Xiang Yang,^a ^* Yue-Zhong Li ^a and Kun Jiang ^a

^aHuai Nan Union University, Huainan, Anhui 232038, People's Republic of China
^*Correspondence e-mail: yang_shengxiang@126.com

(Received 5 December 2008; accepted 22 December 2008; online 8 January 2009)

In the title compound, [Sn₂(CH₃)₆(C₆H₂O₄S)(H₂O)]_n, each of the two crystallographically independent Sn atoms exhibits a distorted trigonal–bipyramidal coordination geometry formed by two O and three C atoms. The coordinated water molecule plays an important role in crystal packing consolidation via O—H⋯O hydrogen bonding.

Related literature

For related structures, see: Prabusankar & Murugavel (2004 ); Bhandari et al. (1998 ); Ma et al. (2006 ).

Experimental

Crystal data

[Sn₂(CH₃)₆(C₆H₂O₄S)(H₂O)]
M_r = 515.74
Monoclinic, P 2₁
a = 7.2761 (16) Å
b = 10.467 (2) Å
c = 12.894 (3) Å
β = 102.768 (2)°
V = 957.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.73 mm⁻¹
T = 298 (2) K
0.40 × 0.30 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.408, T_max = 0.585 (expected range = 0.383–0.549)
4866 measured reflections
3204 independent reflections
2950 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.067
S = 1.03
3204 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.41 e Å⁻³
Absolute structure: Flack (1983 ), 1631 Friedel pairs
Flack parameter: −0.06 (3)

Table 1
Selected bond lengths (Å)

Sn1—C9	2.114 (7)
Sn1—C7	2.117 (7)
Sn1—C8	2.120 (8)
Sn1—O1	2.135 (5)
Sn1—O2ⁱ	2.641 (5)
Sn2—C10	2.108 (7)
Sn2—C12	2.108 (7)
Sn2—C11	2.114 (7)
Sn2—O3	2.178 (4)
Sn2—O5	2.495 (5)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1⋯O3ⁱⁱ	0.85 (8)	2.38 (8)	3.050 (7)	136 (7)
O5—H2⋯O4ⁱⁱⁱ	0.85 (7)	1.98 (8)	2.765 (6)	153 (7)
Symmetry codes: (ii) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+2]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043614/cv2496sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043614/cv2496Isup2.hkl

checkCIF report

Comment top

Organotin complexes are attracting more and more attention because of their considerable structural diversity and interesting topologies (Prabusankar et al., 2004). From the coordinated viewpoint, those dicarboxylate ligands with additional donor atoms, has been revealed to help the construction of interesting topologies (Bhandari et al., 1998). Herein, we report the structure of the title complex, (I).

The title compound (Fig.1) forms an extended one-dimensional chain structure along the b axis arising from Sn—O bridges to ligands. The Sn1 atom has distorted trigonal-bipyramidal geometry, with atoms O1 and O2 in axial positions [O1—Sn1—O2(1 - x, y + 1/2, 1 - z) = 172.06 (17) °] and the C atoms of the three methyl groups in equatorial positions. Associated with the sum of the angles subtended at the Sn1 in the equatorial plane is 357.9 (4) °, indicating approximate coplanarity for these atoms; and the Sn1—O1 distance 2.135 (5) Å and Sn1—O2ⁱ distance 2.641 (5) Å (Table 1), are close to the reported values for organotin compounds (Ma et al., 2006). The environment of the Sn2 atom is approximate to Sn1.

Related literature top

For related structures, see: Prabusankar et al. (2004); Bhandari et al. (1998); Ma et al. (2006).

Experimental top

The reaction was carried out under nitrogen atmosphere. Thiophenn-2,5-dicarboxylic acid (1 mmol) and sodium ethoxide (2 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Trimethyltin chloride (2 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from dichloromethane to yield colourless blocks of compound (yield 82%. m.p.463k). Anal. Calcd (%) for C₁₂H₂₂O₅SSn₂ (Mr = 515.74): C, 27.94; H, 4.30; Found (%): C, 27.65; H, 4.57.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A portion of the polymeric chain of the title compound showing the atomic numbering and 30% probability displacement ellipsoids.
	Fig. 2. One-dimensional polymeric chain in the title compound.

catena-Poly[[aquatrimethyltin(IV)]-{[trimethyltin(IV)]-µ₃-thiophene- 2,5-dicarboxylato}] top

Crystal data top

[Sn₂(CH₃)₆(C₆H₂O₄S)(H₂O)]	F(000) = 500
M_r = 515.74	D_x = 1.788 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.2761 (16) Å	Cell parameters from 3167 reflections
b = 10.467 (2) Å	θ = 2.5–27.3°
c = 12.894 (3) Å	µ = 2.73 mm⁻¹
β = 102.768 (2)°	T = 298 K
V = 957.7 (4) Å³	Block, colourless
Z = 2	0.40 × 0.30 × 0.22 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3204 independent reflections
Radiation source: fine-focus sealed tube	2950 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
T_min = 0.408, T_max = 0.585	k = −12→12
4866 measured reflections	l = −14→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0298P)² + 0.4614P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3204 reflections	Δρ_max = 0.40 e Å⁻³
193 parameters	Δρ_min = −0.41 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1631 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (3)

Crystal data top

[Sn₂(CH₃)₆(C₆H₂O₄S)(H₂O)]	V = 957.7 (4) Å³
M_r = 515.74	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.2761 (16) Å	µ = 2.73 mm⁻¹
b = 10.467 (2) Å	T = 298 K
c = 12.894 (3) Å	0.40 × 0.30 × 0.22 mm
β = 102.768 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3204 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2950 reflections with I > 2σ(I)
T_min = 0.408, T_max = 0.585	R_int = 0.024
4866 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.067	Δρ_max = 0.40 e Å⁻³
S = 1.03	Δρ_min = −0.41 e Å⁻³
3204 reflections	Absolute structure: Flack (1983), 1631 Friedel pairs
193 parameters	Absolute structure parameter: −0.06 (3)
1 restraint

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.40954 (6)	0.66275 (4)	0.52089 (3)	0.05596 (13)
Sn2	0.29616 (5)	−0.21300 (4)	0.94966 (3)	0.04704 (11)
O1	0.2935 (8)	0.5249 (5)	0.6105 (4)	0.0697 (13)
O2	0.4490 (8)	0.3555 (5)	0.5684 (4)	0.0712 (13)
O3	0.2928 (6)	−0.0330 (4)	0.8646 (3)	0.0549 (11)
O4	0.0302 (6)	0.0281 (5)	0.9120 (3)	0.0620 (12)
O5	0.3171 (8)	−0.4236 (5)	1.0422 (5)	0.0697 (14)
S1	0.3024 (2)	0.17295 (16)	0.71215 (11)	0.0493 (3)
C1	0.3378 (10)	0.4063 (7)	0.6153 (5)	0.0571 (16)
C2	0.2486 (8)	0.3306 (5)	0.6871 (4)	0.0463 (14)
C3	0.1297 (10)	0.3741 (7)	0.7489 (6)	0.0668 (19)
H3	0.0850	0.4575	0.7468	0.080*
C4	0.0833 (9)	0.2787 (8)	0.8154 (5)	0.0638 (16)
H4	0.0038	0.2919	0.8618	0.077*
C5	0.1680 (8)	0.1643 (7)	0.8045 (4)	0.0463 (12)
C6	0.1558 (8)	0.0462 (6)	0.8644 (4)	0.0476 (14)
C7	0.2903 (11)	0.5827 (9)	0.3703 (5)	0.079 (2)
H7A	0.3624	0.5094	0.3586	0.118*
H7B	0.2918	0.6451	0.3159	0.118*
H7C	0.1627	0.5574	0.3681	0.118*
C8	0.2492 (14)	0.8103 (8)	0.5708 (8)	0.097 (3)
H8A	0.1767	0.7757	0.6181	0.145*
H8B	0.1657	0.8470	0.5099	0.145*
H8C	0.3324	0.8752	0.6072	0.145*
C9	0.6959 (10)	0.6383 (9)	0.5970 (6)	0.080 (2)
H9A	0.7046	0.5871	0.6597	0.119*
H9B	0.7523	0.7202	0.6166	0.119*
H9C	0.7610	0.5964	0.5495	0.119*
C10	0.0317 (9)	−0.2808 (8)	0.8666 (6)	0.0686 (19)
H10A	−0.0630	−0.2177	0.8689	0.103*
H10B	0.0016	−0.3582	0.8991	0.103*
H10C	0.0361	−0.2974	0.7940	0.103*
C11	0.5359 (11)	−0.2714 (8)	0.8945 (7)	0.084 (3)
H11A	0.4987	−0.3313	0.8374	0.125*
H11B	0.6248	−0.3110	0.9516	0.125*
H11C	0.5931	−0.1982	0.8696	0.125*
C12	0.3463 (10)	−0.1258 (7)	1.1007 (5)	0.0656 (19)
H12A	0.2520	−0.0619	1.1015	0.098*
H12B	0.4686	−0.0867	1.1156	0.098*
H12C	0.3411	−0.1892	1.1538	0.098*
H1	0.405 (12)	−0.434 (8)	1.097 (6)	0.079*
H2	0.233 (11)	−0.442 (8)	1.076 (6)	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0634 (3)	0.0477 (2)	0.0566 (2)	0.0046 (2)	0.0130 (2)	0.0066 (2)
Sn2	0.03417 (18)	0.0448 (2)	0.0646 (2)	0.00064 (19)	0.01612 (16)	0.0085 (2)
O1	0.092 (4)	0.042 (3)	0.081 (3)	0.010 (3)	0.033 (3)	0.019 (2)
O2	0.099 (4)	0.052 (3)	0.073 (3)	0.003 (3)	0.041 (3)	0.002 (2)
O3	0.051 (2)	0.050 (2)	0.070 (3)	0.013 (2)	0.026 (2)	0.018 (2)
O4	0.051 (3)	0.066 (3)	0.075 (3)	0.009 (2)	0.028 (2)	0.014 (2)
O5	0.057 (3)	0.059 (3)	0.099 (4)	−0.003 (2)	0.029 (3)	0.023 (3)
S1	0.0592 (9)	0.0388 (8)	0.0543 (7)	0.0041 (7)	0.0223 (7)	0.0034 (7)
C1	0.065 (4)	0.054 (4)	0.050 (3)	0.002 (3)	0.008 (3)	0.007 (3)
C2	0.049 (3)	0.041 (3)	0.047 (3)	0.005 (2)	0.007 (3)	0.006 (2)
C3	0.069 (5)	0.047 (4)	0.087 (5)	0.019 (3)	0.022 (4)	0.016 (3)
C4	0.066 (4)	0.055 (4)	0.078 (4)	0.016 (4)	0.034 (3)	0.008 (4)
C5	0.042 (3)	0.049 (3)	0.049 (3)	0.007 (3)	0.011 (2)	0.002 (3)
C6	0.040 (3)	0.051 (4)	0.053 (3)	0.004 (3)	0.015 (3)	0.003 (3)
C7	0.067 (5)	0.098 (7)	0.064 (4)	−0.020 (4)	0.000 (4)	0.004 (4)
C8	0.125 (8)	0.051 (5)	0.135 (8)	0.011 (5)	0.073 (7)	0.012 (5)
C9	0.070 (5)	0.086 (6)	0.073 (4)	−0.002 (4)	−0.003 (4)	−0.002 (4)
C10	0.047 (4)	0.075 (5)	0.080 (4)	−0.008 (3)	0.004 (3)	−0.004 (4)
C11	0.071 (5)	0.064 (5)	0.133 (7)	0.024 (4)	0.059 (5)	0.025 (5)
C12	0.060 (4)	0.059 (4)	0.071 (4)	−0.005 (3)	−0.001 (3)	0.011 (3)

Geometric parameters (Å, º) top

Sn1—C9	2.114 (7)	C4—C5	1.368 (10)
Sn1—C7	2.117 (7)	C4—H4	0.9300
Sn1—C8	2.120 (8)	C5—C6	1.470 (9)
Sn1—O1	2.135 (5)	C7—H7A	0.9600
Sn1—O2ⁱ	2.641 (5)	C7—H7B	0.9600
Sn2—C10	2.108 (7)	C7—H7C	0.9600
Sn2—C12	2.108 (7)	C8—H8A	0.9600
Sn2—C11	2.114 (7)	C8—H8B	0.9600
Sn2—O3	2.178 (4)	C8—H8C	0.9600
Sn2—O5	2.495 (5)	C9—H9A	0.9600
O1—C1	1.282 (9)	C9—H9B	0.9600
O2—C1	1.233 (8)	C9—H9C	0.9600
O3—C6	1.296 (7)	C10—H10A	0.9600
O4—C6	1.223 (6)	C10—H10B	0.9600
O5—H1	0.85 (8)	C10—H10C	0.9600
O5—H2	0.85 (7)	C11—H11A	0.9600
S1—C5	1.702 (5)	C11—H11B	0.9600
S1—C2	1.711 (6)	C11—H11C	0.9600
C1—C2	1.474 (9)	C12—H12A	0.9600
C2—C3	1.376 (8)	C12—H12B	0.9600
C3—C4	1.405 (10)	C12—H12C	0.9600
C3—H3	0.9300

C9—Sn1—C7	122.7 (3)	C6—C5—S1	121.5 (5)
C9—Sn1—C8	120.0 (4)	O4—C6—O3	124.0 (6)
C7—Sn1—C8	115.2 (4)	O4—C6—C5	122.2 (6)
C9—Sn1—O1	97.7 (3)	O3—C6—C5	113.8 (5)
C7—Sn1—O1	95.6 (3)	Sn1—C7—H7A	109.5
C8—Sn1—O1	91.0 (2)	Sn1—C7—H7B	109.5
C9—Sn1—O2ⁱ	81.7 (3)	H7A—C7—H7B	109.5
C7—Sn1—O2ⁱ	91.3 (2)	Sn1—C7—H7C	109.5
C8—Sn1—O2ⁱ	82.5 (3)	H7A—C7—H7C	109.5
O1—Sn1—O2ⁱ	172.06 (17)	H7B—C7—H7C	109.5
C10—Sn2—C12	124.6 (3)	Sn1—C8—H8A	109.5
C10—Sn2—C11	117.4 (4)	Sn1—C8—H8B	109.5
C12—Sn2—C11	116.7 (3)	H8A—C8—H8B	109.5
C10—Sn2—O3	97.4 (3)	Sn1—C8—H8C	109.5
C12—Sn2—O3	94.1 (2)	H8A—C8—H8C	109.5
C11—Sn2—O3	89.9 (2)	H8B—C8—H8C	109.5
C10—Sn2—O5	84.1 (3)	Sn1—C9—H9A	109.5
C12—Sn2—O5	87.8 (2)	Sn1—C9—H9B	109.5
C11—Sn2—O5	86.4 (2)	H9A—C9—H9B	109.5
O3—Sn2—O5	176.36 (17)	Sn1—C9—H9C	109.5
C1—O1—Sn1	123.8 (4)	H9A—C9—H9C	109.5
C6—O3—Sn2	118.5 (4)	H9B—C9—H9C	109.5
Sn2—O5—H1	118 (6)	Sn2—C10—H10A	109.5
Sn2—O5—H2	118 (6)	Sn2—C10—H10B	109.5
H1—O5—H2	92 (7)	H10A—C10—H10B	109.5
C5—S1—C2	92.3 (3)	Sn2—C10—H10C	109.5
O2—C1—O1	125.4 (6)	H10A—C10—H10C	109.5
O2—C1—C2	120.3 (6)	H10B—C10—H10C	109.5
O1—C1—C2	114.2 (6)	Sn2—C11—H11A	109.5
C3—C2—C1	127.4 (6)	Sn2—C11—H11B	109.5
C3—C2—S1	110.9 (4)	H11A—C11—H11B	109.5
C1—C2—S1	121.5 (5)	Sn2—C11—H11C	109.5
C2—C3—C4	112.6 (6)	H11A—C11—H11C	109.5
C2—C3—H3	123.7	H11B—C11—H11C	109.5
C4—C3—H3	123.7	Sn2—C12—H12A	109.5
C5—C4—C3	112.7 (6)	Sn2—C12—H12B	109.5
C5—C4—H4	123.7	H12A—C12—H12B	109.5
C3—C4—H4	123.7	Sn2—C12—H12C	109.5
C4—C5—C6	126.9 (5)	H12A—C12—H12C	109.5
C4—C5—S1	111.5 (5)	H12B—C12—H12C	109.5

Symmetry code: (i) −x+1, y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O3ⁱⁱ	0.85 (8)	2.38 (8)	3.050 (7)	136 (7)
O5—H2···O4ⁱⁱⁱ	0.85 (7)	1.98 (8)	2.765 (6)	153 (7)

Symmetry codes: (ii) −x+1, y−1/2, −z+2; (iii) −x, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	[Sn₂(CH₃)₆(C₆H₂O₄S)(H₂O)]
M_r	515.74
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	7.2761 (16), 10.467 (2), 12.894 (3)
β (°)	102.768 (2)
V (Å³)	957.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.73
Crystal size (mm)	0.40 × 0.30 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.408, 0.585
No. of measured, independent and observed [I > 2σ(I)] reflections	4866, 3204, 2950
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.067, 1.03
No. of reflections	3204
No. of parameters	193
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.41
Absolute structure	Flack (1983), 1631 Friedel pairs
Absolute structure parameter	−0.06 (3)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sn1—C9	2.114 (7)	Sn2—C10	2.108 (7)
Sn1—C7	2.117 (7)	Sn2—C12	2.108 (7)
Sn1—C8	2.120 (8)	Sn2—C11	2.114 (7)
Sn1—O1	2.135 (5)	Sn2—O3	2.178 (4)
Sn1—O2ⁱ	2.641 (5)	Sn2—O5	2.495 (5)

Symmetry code: (i) −x+1, y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O3ⁱⁱ	0.85 (8)	2.38 (8)	3.050 (7)	136 (7)
O5—H2···O4ⁱⁱⁱ	0.85 (7)	1.98 (8)	2.765 (6)	153 (7)

Symmetry codes: (ii) −x+1, y−1/2, −z+2; (iii) −x, y−1/2, −z+2.

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of Huai Nan Union University (No. X051040).

References

Bhandari, S., Mahon, M., McGinley, J., Molloy, K. & Roper, C. (1998). J. Chem. Soc. Dalton Trans. pp. 3425–3430. Web of Science CSD CrossRef Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem. 691, 1713–1721. Web of Science CSD CrossRef CAS Google Scholar
Prabusankar, G. & Murugavel, R. (2004). Organometallics, 23, 5644–5647. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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